(1S,2S)-2-{4-[5-(3-tert-butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclopentanecarboxylic acid → 4-{4-[4-(3-tert-Butyl-phenylcarbamoyl)-phenyl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid

HRID 2190663Notes

Reaction equation

HRID 2190663 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:25])[C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O:33][C:34]([C@H:36]1[CH2:41][CH2:40][C@H:39]([C:42](O)=[O:43])[CH2:38][CH2:37]1)=[O:35])C1C=CC=CC=1.C(C1C=C(NC(C2C=CC(N3CCN(C([C@H]4CCC[C@@H]4C(O)=O)=O)CC3)=NC=2)=O)C=CC=1)(C)(C)C>>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:42]([CH:39]4[CH2:38][CH2:37][CH:36]([C:34]([OH:35])=[O:33])[CH2:41][CH2:40]4)=[O:43])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[O:25])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 59317991(1S,2S)-2-{4-[5-(3-tert-butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclopentanecarboxylic acidHCID 59318141N-(3-tert-Butyl-phenyl)-4-piperazin-1-yl-benzamideHCID 178525735HCID 178525735, compound

Product 1

HCID 593180404-{4-[4-(3-tert-Butyl-phenylcarbamoyl)-phenyl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid

Procedure

4-{4-[4-(3-tert-Butyl-phenylcarbamoyl)-phenyl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid was prepared from N-(3-tert-butyl-phenyl)-4-piperazin-1-yl-benzamide and trans-1,4-cyclohexane dicarboxylic acid monobenzyl ester in a manner similar to the one described in the synthesis of (1S,2S)-2-{4-[5-(3-tert-butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclopentanecarboxylic acid above. HRMS m/z calcd for C29H37N3O4 [M+H]: 492.2857. Found: 492.2855.

Sources & evidence

ORD record
ord-af918eaf22a0401eaa1ce6cff83b0a79
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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